1. Diane Halfin (Diane von Furstenberg)
Though Diane von Furstenberg is an American citizen today, she was actually born in Belgium, known then by her maiden name, Halfin. Furstenberg’s story is a remarkable one, as just one and a half years prior to her birth, her mother was a prisoner in the infamous Auschwitz concentration camp.
Growing up, Halfin attended Madrid University before transferring to the University of Geneva where met her future husband, Prince Egon von Furstenberg. She and the German aristocrat quickly fell in love, wasting little time to tie the knot, though they didn’t quite ride off into the sunset for a happily ever after.
In 1970, a year after the Furstenbergs’ royal wedding, Diane decided she would forge a path of her own rather than being known simply for marrying royalty. That’s when she began her career in the fashion industry.
While Furstenberg saw her career as a women’s fashion designer flourish, her marriage to the prince was trending in the opposite direction.
She and Prince Egon divorced in 1983 and shortly after, Furstenberg — she kept the royal surname — was off to New York to continue building her fashion empire.
With two loving children from her marriage, Furstenberg established her fashion company, DvF, in Manhattan and around the globe as one of the top brand names in the fashion.
Born in Washington D.C., Lisa Najeeb Halaby was the great granddaughter of a Syrian immigrant. After earning a Bachelor’s degree in architecture and urban planning from the esteemed Princeton University, her career took her to the Middle East, as her heritage lent a heightened interest to her roots.
After working at a new job with Jordan’s Alia Airlines, she met the Hussein bin Talal, King of Jordan. She befriended Hussein — who was still mourning his third wife’s death from a helicopter crash — through work, but that quickly budded into a romance. They wed in 1978 and remained together until his passing in 1999.
3. Rita Hayworth
When it comes to leaving a lasting impression, there really isn’t anything more Rita Hayworth could’ve done to fulfill what was an incredibly memorable and lavish life. There are few women or men who have reached the level of celebrity Hayworth did through her work as an actress, dancer and model.
Through the height of her popularity in the 1940s, America’s most iconic pin-up girl only belonged to one man… well, we should probably clarify that. The most sought after beauty only belonged to one man during World War II: Edward C. Judson. Actually, let’s backtrack that.
That swarmy fellow who doubled her in age was only married to Hayworth for five years until she divorced him in 1942. Still a ways away from royalty…
Roughly 18 months after Hayworth’s first husband took almost all of her money, she married another man who left his own mark in history and the arts, the great Orson Welles.
Once again, the marriage left Hayworth far from being a happy wife, as their rushed wedding (announced just the day prior) proved to be a telling sign of times to come.
The couple had a daughter, but it seemed that a domestic life for the wildly famous pair wasn’t written in the stars. The two divorced in November 1947. Hayworth moved fast with the times and, by the following year, she had already decided to leave her fantastic acting career behind to pursue her new romance with Prince Aly Khan…
Hayworth and Prince Aly Khan got hitched in 1949, but it turns out that the third time isn’t always the charm when it comes to weddings. Just like her last two marriages, Hayworth found her husband to be stifling and not at all the man she thought she had married.
After giving birth to a daughter, things quickly went south in 1951 when Prince Khan was spotted dancing with actress Joane Fontaine, and at the same nightclub they had met!
Hayworth packed her bags and was off to Lake Tahoe, staying there with her daughter until what was a very ugly divorce process was finalized in January 1953.
The royal wedding was not the last of Hayworth’s marital troubles, as she endured another two failed marriages. Not even the most seemingly perfect life is all it appears on the surface.
4. Alice Heine
Born in 1858 in New Orleans, Alice Heine lived a fascinating life for what was already a remarkable point in history. Although she was born to a Jewish family, she converted to Christianity when she married Armand Chapelle de Jumilhac, 7th Duke of Richelieu, in 1875.
After having a son and daughter, the two separated. In 1889, Heine once again caught the eye of royalty, this time Prince Albert I, Prince of Monaco. Once again, sharing a life with royalty proved to have its difficulties, as the two separated in 1902 despite remaining married by law.
When all was said and done, Heine had quite an interesting run at the royal throne, having been married to two Dukes, the second of which would become a prince, making her a princess.
5. Christopher O’Neill
Christopher O’Neill was born in London and lived much of his early life there along with Austria and Germany. Despite that, his father’s American heritage made him a dual citizen in Britain and America. O’Neill’s sweeping success as a partner at Noster Capital almost came to a screeching halt when it was revealed that he was seeing Princess Madeleine, Duchess of Halsingland and Gastrikland of the Swedish throne.
If he was to be allowed to marry the Swedish princess, he would have to completely give up all his investments involved in the Stockholm Stock Exchange, which turned out to be a third of the company’s sales!
Love triumphed over wealth, as O’Neill relinquished his role to be with Princess Madeleine, a decision that has yielded three beautiful children since their royal wedding in 2013.
6. Meghan Markle
Before one fateful blind date changed everything in June 2016, Meghan Markle was enjoying a flourishing acting career. It took years of hard work to achieve her Hollywood dream before landing a star role on the hit legal drama Suits, but her time on screen quickly reached a finish line when she found a new life path in England.
What began as one blind date with Prince Harry, Duke of Sussex, quickly blossomed into something much more.
By November 2017, it was announced that Markle and Prince Harry were engaged. To focus on her new life and becoming a British citizen, Markle announced she would step away from her acting career, leaving her social media behind in the process. (Now that’s dedication.)
Markle’s engagement to Prince Harry marked a momentous occasion for the British royal throne, as she is of mixed race. The progressive attitude of the royal family in vehemently defending her and Prince Harry’s love sent a message to the world that antiquated ideas on marriage and relationships were no longer the norm for the British monarchy.
The wedding ceremony took place in May 2018 at St. George’s Chapel at Windsor Castle and was brimming with celebrities from around the world there to witness Ms. Markle become the Duchess of Sussex. The Duchess likely never could’ve imagined being a part of such an extravagant celebration of love, as back in 2011, she had just tied the knot with fellow actor Trevor Engelson.
Safe to say that hope was far from lost when she and Engelson separated in 2013.
7. Grace Kelly
It seemed like as soon as Grace Kelly began her acting career in 1950, she was already one of the most recognizable and beloved actresses in the world.
Brief as her career was, Kelly was in some of the biggest Hollywood films of the time. She starred in numerous Alfred Hitchcock films, and shared the screen with great names like Frank Sinatra, Mickey Rooney and Bing Crosby.
As famous as Kelly was on-screen, the blonde-haired beauty carved out a modeling career that was every bit as impressive. But that all came to end in 1956. In April of that year, the Golden Globe winning actress married the man of her dreams: Rainier III, Prince of Monaco.
While at the 1955 Cannes Film Festival, Kelly was invited to meet Prince Rainier for a photo session. Despite dating a French actor at the time, the meeting developed into a year of courting that concluded with a wedding. Well, more like two… a civil and religious ceremony (as required by The Napoleonic Code of Monaco).
The newly named Princess of Monaco left her Hollywood fame to build a royal family, giving birth to two girls and one boy.
Everything played out as perfect as the pictures until one fateful day in September 1982, the Princess was driving her daughter through the mountains of Monaco when she suffered a stroke, and veered her vehicle off a cliff.
The princess passed the following day, but her prince remained true to his love, never remarrying until he was laid to rest by her side in 2005.
8. Marie-Chantal Miller
Marie-Chantal Miller had just finished was pursuing a degree in History of Art at the prestigious New York University when a sudden change in plans in 1993 led her down a path to become a part of history.
In 1992, a blind date set Miller up with Pavlos, Crown Prince of Greece.
Fast forward a year: Miller and Pavlos were on holiday in Switzerland for Christmas when the prince proposed atop a ski lift.
Their wedding in July 1995 was the definition of extravagance with 1,400 guests (the most since Queen Elizabeth II and Prince Philip’s marriage) and is believed to have cost upwards of $8 million!
9. Sarah Butler
Houston native Sarah Butler — a strong-minded voice for maternal and newborn health — found the man of her dreams in Prince Zeid bin Ra’ad Zeid al-Hussein of Jordan, Crown Prince of Iraq.
There was no doubt the two were perfect for one another, as Prince Zeid has been a prominent figure an array of global human rights positions for decades.
Their royal wedding was held in July 2000, making Butler’s new title Princess Sarah Zeid of Jordan.
Together, this royal couple has continued their individual missions for human rights in a variety of facets, using their positions of power for the greater good of humanity.
10. Alexandra Miller
Entrepreneurial billionaire and creator of duty-free shopping Robert Miller was living in New York City with his daughter Alexandra just a couple floors above some other royalty that made the list in the von Furstenbergs.
It was here that young love bloomed when Miller met a teenage Prince Alexander von Furstenberg in the early ‘90s.
She and Prince Alexander quickly fell in love, marrying in October 1995 after only a couple years of dating.
There wedding ceremony wasn’t far from home, choosing the Church of St. Ignatius Loyola in Upper Manhatten. By 2001, Princess Alexandra von Furstenberg had two children with her royal husband.
Unfortunately, like mother (in law), like daughter. Fast as the royal couple married and built a family, they found that they were not the perfect pair they initially thought they were. By 2002, the Princess Sarah and Prince Alexander had separated, divorcing later that year.
This did not mark the last time the former princess would find love. After dating for some time, von Furstenberg found a match in designer Dax Miller, marrying her second husband in 2015. Though she may no longer be royalty, her children, Princess Talita and Prince Tassilo, will carry on her royal legacy.
11. John Owen Dominis
Sadly, the story of John Owen Dominis’ rise to royalty is a pretty far cry from that of a Disney Princess. Dominis was the son of an Italian sea captain who often voyaged across the Pacific to America, stopping in Hawaii frequently. Though Dominis was born in New York (1832), he left at a young age to settle in Hawaii (1837).
Dominis grew up in Honolulu, attending a school next to the Royal School where he befriended Hawaiian children who were princes and princesses. Dominis would eventually marry Lydia Kamak’eha Paki in 1862, who would eventually don the title of Queen Lili’uokalani, but there marriage was far from perfect…
Queen Lili’uokalani wanted to have children but was unable to do so. To make matters worse, Dominis was brazenly unfaithful, having casual extramarital affairs with his servants. That resulted in an illegitimate son. Despite the cruel reality, Queen Lili’uokalani welcomed him as her own.
Though Lili’uokalani was the last monarch to rule over Hawaii before it was constitutionalized as part of the United States, she was only actually queen when her brother, King Kalakaua died on in January 1891. If there’s any solace in what was an otherwise sad story for her, it’s that Dominis was only the husband to the royal throne for seven months before his own death.
12. Kendra Spears
Born and raised in the Pacific Northwest, Seattle native Kendra Spears was destined for a future far brighter than the eternal overcast of the PNW.
After graduating college, Spears was off to the East Coast to begin her modeling career in NYC.
Spears’ modeling took her all over the globe. All eyes were on Spears, as she regularly appeared on the cover of fashion magazines, but she only had eyes for one, Prince Rahim Aga Khan. The two married in August 2013, making Ms. Spears “Princess Salwa Aga Khan.” The royal couple had their first child in 2015 and two years later, Princess Salwa gave birth to their second son.
13. Julie Elizabeth Huston Ongaro
Prince Robert of Luxembourg followed in his mother’s, Joan Douglas Dillion (another name on this list), and father’s, Princes Charles of Luxembourg, footsteps. At least, he did so in following his heart to marry an American woman.
Prince Robert was in the United States studying at Georgetown University, which is how he met Julie Elizabeth Huston Ongaro.
The couple first met in 1987 and took things nice and slowly. They married in Massachusetts in 1994. Despite how long they were together, Prince Robert never went through the formal process of asking for consent, so the Princess of Nassau was not officially given her title until 2004.
14. Ariana Austin
Ariana spent much of her life in Washington D.C. After attending Fisk University and earning a master’s degree at Harvard, she returned to D.C. to teach at Georgetown University, becoming the first African-American full-time professor at the university in the process.
It was also in the nation’s capital that she met Prince Joel Dawit Makonnen of Ethiopia at a nightclub in 2005. The two hit it off and began dating and steadily dated until the prince proposed to her in 2014.
Three years later, Austin converted to Islam before their royal wedding in nearby Maryland. A royal wedding of epic proportions, the ceremony lasted five days!
15. Caroline Bouvier
When Jackie Bouvier married (future) President John F. Kennedy, she became a part of what is considered to be one of the few American “royal” families. Insanely powerful as the Kennedy family was, it was her sister, Caroline “Lee” Bouvier, who truly married royalty.
That chapter of her life didn’t come until later, though. First, Bouvier fell in love with publishing executive Michael Temple Canfield. They married in 1953, but their rocky relationship only lasted until a divorce was finalized in 1959.
Clearly, her marriage with Canfield had fallen apart well before their divorce in 1959 given that she got remarried the same year to Polish Prince Stanislaw Albrecht Radziwill, Ordinat of Olyka.
After marrying, her title became Her Serene Highness Princess Stanislaw Albrecht Radziwill.
Together, they had two children, one boy and one girl. While the princess was on her second marriage, her prince was on his third. It turned out the third time was not the charm, as they eventually divorced in 1974. In fact, that went for her too, because she again remarried actor and producer Herbert Ross in 1988 only to divorce again in 2001.
16. Kelly Rondestvedt
It makes sense that Kelly Rondestvedt’s father was a pilot for the United States Navy, because she had her fair share of travel before finding her royal significant other.
Born in Florida, Rondestvedt move out west to California at an early age where she would eventually graduate from UCLA and build a successful career as an investment banker.
While on a trip to New York in 2007, a chance encounter with Hubertus, Hereditary Prince of Save-Coburg and Gotha grew into a lasting love. In 2009 it was off to Germany where a wedding ceremony at Callenberg Castle (and again at St. Motiz Church two days later) made Ms. Rondestvedt “Hereditary Princess of Saxe-Coburg and Gotha, Duchess of Saxony.”
17. Wallis Simpson
Blue Ridge Summit is a tiny little unincorporated community in southern Pennsylvania bordering Maryland. Even today, it has less than 1,000 people living there, but one very important person was born here in 1896 – Wallis Simpson.
Born “Bessie Wallis Warfield,” she would live the first 40 years of her life as another face in the crowd before the extraordinary happened.
Her first marriage was to Earl Spencer Jr. in 1916, which was rife with separations until they finally divorced in 1927.
Shortly thereafter, she met Ernest Simpson, whom she married in 1928. It was a new name and face, but the same story. After another 11 years, she called it quits, though this time under VERY different circumstances…
Back in 1931 while in London, a friend had introduced Wallis to Prince Edward VIII, Duke of Windsor. The two saw each other for years and she was rumored to be the prince’s mistress.
Those rumors were corroborated when George V died in 1936 and Prince Edward VIII was set to take the throne.
It was an international crisis when he sought abdication from his 11-month tenure as King Edward VIII, wanting to marry (the still married) Wallis. While he passed on the throne to follow his heart, she got her divorce to marry and become the Duchess of Windsor.
The scandalous decision was filled with controversy that went far beyond a disapproved marriage. Nonetheless, the two remained married until the Duke’s death in 1972.
18. Hope Cooke
Born in San Francisco (1940), Hope Cooke was halfway across the world from the throne where she would eventually take as queen.
During Cooke’s freshman year at Sarah Lawrence College (NY), she took a summer trip to India where she would meet Palden Thondup Namgyal, Crown Prince of Sikkim in the lounge of their hotel.
The prince was almost twice her age and a recent widower with three children. Clearly, none of that mattered — just two years later, they were engaged, only waiting an extra year due to foreboding astrological signs.
That wasn’t quite enough, because while he became king and she became Queen of Sikkim, their 17-year marriage was a tumultuous ride.
Throughout their marriage, both sides had affairs. To make matters worse, King Namgyal was the last of his line to rule, as Sikkim became a part of India effectively abolishing his monarchy.
Although they had two children together, they eventually separated and Cooke moved back to NYC.
Although she lived in NYC, Cooke was not actually a citizen, leaving her feeling like a person without a country. A divorce was finalized in 1980, only for Namgyal to come to NYC for cancer treatment where he would pass away in 1982.
Cooke would remarry in 1983, though her relationship with Pulitzer Prize-winning historian Mike Wallace would also end in divorce.
19. Joan Douglas Dillon
New York City’s own, Joan Douglas, may be on a list of Americans, but she has the distinct honor of marrying royalty not once, but twice!
Before either of these royal marriages, she was married to another man from 1953-63.
In 1967, Dillon married Prince Charles of Luxembourg and lived happily together until his death in 1977. She then remarried shortly after in 1978 to Philippe de Noailles, Duke de Mouchy, until his death in 2011. These two marriages gave her the long title of Princess Charles of Luxembourg, Duchess of Mouchy and Poix.
20. Anita Stewart Morris
Anita Stewart was born in New Jersey in 1886. She left America and married Prince Miguel, Duke of Viseu of the House of Braganza in Austria-Hungary. Together, they had three children and lived happily until his death in 1923.
After her husband’s passing, the Princess Miguel of Braganza, Duchess of Viseu returned to America, but had to officially relinquish her royal title (though everyone still used her regal moniker).
It wasn’t until over 20 years later that she remarried (1946), remaining with her second husband at their Newport estate until his death in 1967.